No matter how old we get, our parents’ and grandparents’ stories continue to guide us through major life decisions. When we’re sitting with client families, we hear this often. Clients wondering, “What would mom say?” or “What would dad do?”
When you think about your financial legacy, passing down your values and family history are just as important as the documents in your estate plan.
Don’t leave them wondering what you would do or why.
The holiday season is the perfect time to have these conversations with your loved ones.
To make it easier for you, here are two printable lists of questions.
- “Top 10 Questions to Ask Someone You Love: Legacy & Wealth Edition”
- “Life Interview Questions” by Brendon Burchard
As you’re sitting around the dinner table, pick a few, press record, and capture the wisdom for future generations.
Transcript:
Welcome back to Lizzie’s Wealth Wisdoms. Before we dive in today, I want to start with a personal video. Eight years ago, during the holidays, I filmed a short interview with my Grammie who was 94 years old at the time.
[Video Clip]
Lizzie: -have you tell us your biggest piece of advice. After 92 years, what have you learned the most?
Grammie: What have I learned the… Well, I have to tell you that in secret.
[laughter]
Carl: What’s all these secrets about? Just spit it out.
[laughter]
Grammie: I don’t- I don’t tell all of these secrets.
Carl: Well, it must be- must be X-rated.
Grammie: Well.
Lizzie: Could be.
Grammie: I don’t know.
It makes me smile every time I watch it. Not because it’s perfect or polished, but because it is her. Her voice, her humor, her presence. And now my boys can hear their great grandmother in a way that no retold story could recreate. I share this because it captures the heart of today’s message.
The Holidays: A Rare Multi-Generational Moment
This time of year is one of the only moments when families naturally gather across multiple generations—grandparents, parents, adult children, even teenagers and young kids all under one roof. And when I sit with families in practice, especially during big life decisions—a health scare, a job transition, a financial turning point—I often hear,
“I wish mom were here. She’d know what to tell me.”
“Dad would have had the perfect advice.”
Legacy isn’t just the assets we leave. It’s the voice, the value, the wisdom that guides future decisions—financial and otherwise. And the holidays give us a unique chance to preserve both.
Why These Conversations Matter for Family Wealth
Family wealth rarely lasts for multiple generations by accident. It lasts because:
- Values are communicated.
- Stories are shared.
- The “why” behind the wealth is passed down, not just the “what.”
- And families take time to articulate their hopes for how that wealth should support future generations.
Many families have beautifully constructed plans—trusts, 529s, charitable investment vehicles, investment strategies. But without capturing the family history behind the wealth and how it was created, what sacrifices were made, what values guided those decisions, the next generation is left without a compass.
Your stories become the framework that helps your children and grandchildren steward wealth wisely.
This Holiday Season: Start With One Conversation
This holiday season, start with one conversation. It doesn’t have to be formal. Sit with someone you love—a parent, grandparent, aunt, uncle, sibling—and ask:
- How did our family build its financial foundation?
- What opportunities shaped your life?
- What financial choices were the hardest?
- How did you think about education, charitable giving, or investing in a business? And does your perspective differ today?
- What values do you hope guide our family’s decisions in the future?
And then record it. A voice memo or a video clip is perfect. These conversations become just as important as the documents in your estate plan. They are the emotional and philosophical blueprint behind the financial one.
Downloadable Resources: Two Simple Ways to Begin
I’ve created two PDFs to help you start—whether your focus is on storytelling, values, or multi-generational planning.
- “The Top 10 Questions to Ask Someone You Love: The Legacy & Wealth Edition”: This is a blend of classic life story questions plus financial value prompts, such as:
-
- What do you hope future generations will remember about how our family wealth began?
- How did you decide what to prioritize financially—education, giving, investing?
- Who did you trust for advice when making big decisions?
- “Life Interview Questions” by Brendon Burchard: A thoughtful list of 32 prompts about experiences, memories, and values. This is not necessarily financial-focused, but it is a great list to peruse for ideas.
Choose a few. Press record. And then capture the wisdom while the wisdom-givers are here.
Closing
In closing, one day your children or grandchildren will face a decision, a career crossroads, a financial choice, a life transition—and they’ll think:
“What would mom say?”
“What would dad do?”
“What advice would granddad give me right now?”
And because you have preserved these stories and the values behind your family’s wealth, they won’t have to wonder.
Legacy is more than assets. It’s the voices, the values and the vision that we pass forward. Thank you for listening to Lizzie’s Wealth Wisdoms. Until next time.
